Optically clear aminosilicone compositions

ABSTRACT

The optically clear compositions comprising 
     (A) an organopolysiloxane which contains at least one monovalent SiC-bonded radical with primary, secondary and/or tertiary amino groups, 
     (B) 0.01 to 1 part by weight per 100 parts by weight of organopolysiloxane (A) of a group of compounds consisting of water, methanol and ethanol and 
     (C) 0.05 to 20 parts by weight of a solubilizing agent per 100 parts by weight of organopolysiloxane (A), chosen from a group consisting of 
     (C1) C 1  - to C 19  -carboxylic acid C 1  - to C 12  -alkyl esters and -glycol esters, 
     (C2) C 3  - to C 20  -alkanols and C 3  - to C 20  -alkanol-C 1  - to C 12  -alkoxylates and 
     (C3) organosilicon compounds containing glycoside radicals.

FIELD OF INVENTION

The present invention relates to optically clear compositions based onan organopolysiloxane containing aminoalkyl groups, water, an alkanoland a solubilizing agent and the preparation thereof.

BACKGROUND OF INVENTION

Organopolysiloxanes containing aminoalkyl groups are employed as textiletreatment agents, in the cosmetics industry and as release agents.

GB-A-20 36 052 describes organopolysiloxanes containing aminoalkylgroups which are formed when a polydimethylsiloxane containing terminalsilanol groups and an alkoxysilane containing aminoalkyl groups aremixed at room temperature. However, the organopolysiloxane containingaminoalkyl groups prepared in this manner is cloudy since the alkanolformed as a condensation product and, optionally, water have limitedsolubility in the organopolysiloxane. On storage, further alkanol andwater are formed during condensation reactions which proceed slowly, thesiloxane chains are lengthened and an alkanol/water phase finallyseparates out. Accurate metering of the organopolysiloxane containingaminoalkyl groups is possible only after separation of the phases oremulsification thereof.

The separating out of alkanol and water can be avoided if the mixture isheated during preparation, in order to complete the reaction and at thesame time drive off the alkanol and water. The removal in vacuo of themethanol formed in the reaction of silanols with methoxysilanecontaining aminoalkyl groups is described in G. Helary and G. Sauvet,Eur. Polym, J. Volume 28, No. 1 pages 37 to 41, 1991.

SUMMARY OF INVENTION

The present invention is based on providing compositions with the leastpossible expenditure, compositions which are based on organopolysiloxanecontaining aminoalkyl groups wherein cloudiness does not occur duringstorage and the organopolysiloxane containing aminoalkyl groups caneasily be metered.

The present invention relates to optically clear compositionscomprising:

(A) an organopolysiloxane which contains at least one monovalentSiC-bonded radical with primary, secondary and/or tertiary amino groups,

(B) 0.01 to 1 part by weight per 100 parts by weight oforganopolysiloxane (A) of a group of compounds consisting of water,methanol and ethanol and

(C) 0.05 to 20 parts by weight of a solubilizing agent per 100 parts byweight of organopolysiloxane (A), chosen from a group consisting of

(C1) C₁ - to C₁₉ -carboxylic acid C₁ - to C₁₂ -alkyl esters and -glycolesters,

(C2) C₃ - to C₂₀ -alkanols and C₃ - to C₂₀ -alkanol-C₁ - to C₁₂-alkoxylates and

(C3) organosilicon compounds containing glycoside radicals.

For most applications, the optically clear composition is processed asan aqueous emulsion. The solubilizing agents do not have a troublesomeeffect during the emulsification and fulfills the function of anemulsifier or an emulsifying auxiliary. A single compound can beemployed as the solubilizing agent, and mixtures of differentsolubilizing agents can also be employed.

In general no more than 0.5 part by weight per 100 parts by weight oforganopolysiloxane (A) of compounds (B) which are chosen from water,methanol and ethanol are present in the optically clear compositions.

Preferably, the organopolysiloxane (A) in the composition contains atleast one siloxane unit of the formula

    R.sup.1.sub.a Q.sub.b SiO.sub.(4-a-b)/2                    (I)

and all other siloxane units have the formula

    R.sup.1.sub.c SiO.sub.(4-c)/2                              (II)

in which

R¹ is identical or different monovalent optionally fluorine-, chlorine-or bromine-substituted C₁ - to C₁₈ -hydrocarbon radicals, hydrogenatoms, C₁ - to C₁₂ - alkoxy or hydroxyl radicals or alkylglycolradicals,

Q is a group of the formula

    --R.sup.2 --[NR.sup.3 (CH.sub.2).sub.m ].sub.d N(R.sup.3).sub.2 (III)

in which

R² is a divalent C₁ - to C₁₈ -hydrocarbon radical,

R³ is a hydrogen atom or an optionally fluorine-, chlorine- or bromine-or C₁ - to C₅ -alkoxy-substituted C₁ - to C₁₈ -hydrocarbon radical,

a has the values 0, 1, or 2,

b has the values 1, 2 or 3,

c has the values 0, 1, 2 or 3,

d has the values 0, 1, 2, 3 or 4 and

m has the values 2, 3, 4, 5 or 6

and the sum of a+b is not more than 4.

The C₃ - to C₁₂ -alkoxy radicals R¹ are of such low reactivity that theC₃ - to C₁₂ -alkanols formed therefrom by condensation with silanolgroups or hydrolysis with water can be obtained only in a very smallmount. Furthermore, these alkanols dissolve readily in theorganopolysiloxane (A) and are themselves solubilizing agents (C1).

Examples of C₁ - to C₁₈ -hydrocarbon radicals are alkyl radicals, suchas the methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl,tert-butyl, n-pentyl, iso-pentyl, neo-pentyl and tert-pentyl radical;hexyl radicals, such as the n-hexyl radical; heptyl radicals, such asthe n-heptyl radical; octyl radicals, such as the n-octyl radical andthe isooctyl radicals, such as the 2,2,4-trimethylpentyl radical; nonylradicals, such as the n-nonyl radical; decyl radicals, such as then-decyl radical; dodecyl radicals, such as n-dodecyl radical; cycloalkylradicals, such as cyclopentyl, cyclohexyl and cycloheptyl radicals andmethylcyclohexyl radicals; aryl radicals, such as the phenyl and thenaphthyl radicals; alkaryl radicals, such as o-, m- and p-tolylradicals, xylyl radicals and ethylphenyl radicals; and aralkyl radicals,such as the benzyl radical and the α- and the β-phenylethyl radical.

The above hydrocarbon radicals R¹ optionally contain an aliphatic doublebond. Examples are alkenyl radicals, such as the vinyl, allyl,5-hexen-1-yl, E-4-hexen-1-yl, Z-4-hexen-1-yl, 2-(3-cyclohexenyl)-ethyland cyclododeca-4,8-dienyl radical. Preferred radicals R¹ with analiphatic double bond are the vinyl, allyl and 5-hexen-1-yl radical.

Preferably, not more than 1% of the hydrocarbon radicals R¹ contain adouble bond.

Examples of C₁ - to C₁₈ -hydrocarbon radicals which are substituted byfluorine, chlorine or bromine atoms are the 3,3,3-trifluoro-n-propylradical, the 2,2,2,2',2',2'-hexafluoroisopropyl radical, theheptafluoroisopropyl radical and the o-, m- and p-chlorophenyl radical.

Examples of the divalent C₁ to C₁₈ -hydrocarbon radicals R² aresaturated straight- or branched-chain or cyclic alkylene radicals, suchas the methylene and ethylene radical, as well as propylene, butylene,pentylene, hexylene, 2-methylpropylene, cyclohexylene and octadecyleneradicals or unsaturated alkylene or arylene radicals, such as thehexenylene radical and phenylene radicals, the n-propylene radical andthe 2-methylpropylene radical being more preferred.

The alkoxy radicals are the alkyl radicals described above bonded via anoxygen atom. The examples of alkyl radicals also apply in their fullscope to the alkoxy radical R¹.

The alkylglycol radicals R¹ preferably have the formula

    --R.sup.2 --[O(CHR.sup.3).sub.d ].sub.n OR.sup.4           (IV)

in which

R², R³ and d have the above meanings,

n is from 1 to 100 and

R⁴ is a hydrogen atom, a radical R³ or a group of the formula ##STR1##in which R⁵ is the radical R³ or O--R³.

Preferably, in the above formulae (I) to (IV),

R¹ is a methyl, phenyl, C₁ - to C₃ -alkoxy or hydroxyl radical or aradical of the formula (IV),

R² is a divalent C₂ - to C₆ -hydrocarbon radical,

R³ is a hydrogen atom or a methyl radical,

a has the values 0 or 1,

b has the value 1,

c has the values 2 or 3 and

d has the value 1.

Linear polydimethylsiloxanes which optionally contain C₁ - to C₃ -alkoxyor hydroxyl end groups are more preferred. In these polymethylsiloxanes,Q is preferably an H₂ N(CH₂)₂ NH(CH₂)₃ - or H₂ N(CH₂)₂ NHCH₂CH(CH₃)CH₂ - group.

The ratio of siloxane units of formula (I) to siloxane units of formula(II) is preferably 1:10 to 30,000, in particular 1:20 to 300. The aminecontents are preferably 0.01 to 2 mequivalents/g, in particular 0.1 to0.7 mequivalents/g, measured as the consumption of 1N hydrochloric acidin ml/g of organopolysiloxane (A) during titration to the neutral point.

One type of organopolysiloxane (A) can be employed. However, it is alsopossible to employ a mixture of at least two different types oforganopolysiloxane (A).

The organopolysiloxane (A) or a mixture of at least two different typesof organopolysiloxane (A) preferably has an average viscosity of 20 to100,000 mPa.s, in particular 20 to 10,000 mPa.s, at 25° C.

The composition preferably comprises 0.1 to 10 parts by weight, inparticular 0.5 to 3 parts by weight, of solubilizing agent (C) per 100parts by weight of organopolysiloxane (A).

The organopolysiloxanes are prepared from

(E) compounds which are chosen from

(E1) organosilanes which contain at least one monovalent SiC-bondedradical with primary, secondary and/or tertiary amino groups and atleast one C₁ - to C₄ -alkoxy group and

(E2) organopolysiloxanes which contain at least one monovalentSiC-bonded radical with primary, secondary and/or tertiary amino groupsand at least one C₁ - to C₄ -alkoxy and/or silanol group and

(F) compounds which are chosen from

(F1) organosilanes which contain at least one C₁ - to C₄ -alkoxy groupand

(F2) organopolysiloxanes which contain at least one C₁ - to C₄ -alkoxygroup and/or silanol group.

The organosilanes (E1) preferably have the formula

    Q.sub.e R.sup.6.sub.f SiR.sup.1.sub.(4-e-f)                (V)

in which

R⁶ is a C₁ - to C₂ -alkoxy radical,

e has the values 1, 2 or 3, preferably 1,

f has the values 1, 2 or 3 and with the proviso that the sum of e+f isnot more than 4, and Q and R¹ have the above meanings.

Preferably, the organopolysiloxane (E2) contains at least one siloxaneunit of above formula (I) and at least one siloxane unit of the formula

    R.sup.1.sub.g R.sup.6.sub.h HO.sub.i SiO.sub.(4-g-h)/2     (VI)

and all other siloxane units have the above formula (II), wherein

g has the values 0, 1 or 2,

h has the values 1, 2 or 3 and

i has the values 0 or 1, with the proviso that the sum of g, h and i isnot more than 3, and Q, R¹ and R⁶ have the above meanings.

The organosilanes (F1) preferably have the formula

    R.sup.6.sub.j SiR.sup.1.sub.(4-j)                          (VII)

in which

j has the values 1, 2, 3 or 4 and

R¹ and R⁶ have the above meanings.

Preferably, the organopolysiloxanes (F2) contain at least one siloxaneunit of above formula (VI) and all other siloxane units have the aboveformula (II).

The organopolysiloxanes (E2) and (F2) preferably have an averageviscosity of 10 to 100,000 mPa.s, preferably 20 to 10,000 mPa.s, inparticular 50 to 1000 mPa.s, at 25° C.

The organopolysiloxanes (A) are preferably prepared at 0° C. to 50° C.,in particular at 10° C. to 30° C.

The reaction time in which 99 mole % of the starting compound (E) and(F) have reacted to give organopolysiloxanes (A) is usually 1 hour to 20days, in particular 12 hours to 3 days.

Preferably, 0.1 to 10 parts by weight, in particular 0.5 to 3 parts byweight, of solubilizing agent (C) are added per 100 parts by weight ofstarting compounds (E) and (F).

The optically clear compositions are preferably prepared by reacting thestarting compounds (E) and (F) in the presence of

(C) 0.01 to 20 parts by weight of the solubilizing agent described aboveper 100 parts by weight of starting compounds (E) and (F).

In this embodiment, the starting compounds (E) and (F) can be mixed withthe solubilizing agent (C) and the optically clear compositions thenform during storage and transportation. It is possible for the reactionmixture of the starting compounds (E) and (F) with the solubilizingagent (C) to be introduced directly into vessels, such as canisters,drums or tanks. After the required reaction time at the requiredreaction temperature, the optically clear compositions which have formedcan be further processed. The required reaction time can be met on thetransportation route or during warehousing.

Thereafter, the starting compounds (E) and (F) can be present in smallamounts in the optically clear compositions. As long as the reaction ofthe starting compounds (E) and (F) has not yet been concludedcompletely, alkanols having 1 to 4 carbon atoms and/or water are stillformed.

One water molecule is formed in the condensation reaction between twosilanol groups. One alkanol molecule is formed in the condensationreaction between one silanol group and one alkoxy group. In thecondensation reaction between two alkoxy groups, one water molecule isrequired and two alkanol molecules are formed.

If the compounds (E) and (F) employed contain more alkoxy groups thansilanol groups, water must be added. The amounts of water required areso low that, because of the solubilizing agent (C) employed, they arehomogeneously miscible with the compounds (E) and (F). A maximum of 0.3,in particular 0.1, part by weight per 100 parts by weight of compounds(E) and (F) is sufficient.

The organopolysiloxanes (E2) and F2) preferably contain silanol groups,since the reaction between silanol groups and alkoxy groups proceedsrapidly.

The optically clear compositions can also be prepared by mixing

(A) an organopolysiloxane which contains at least one monovalentSiC-bonded radical with primary, secondary and/or tertiary amino groups,and

(B) 0.01 to 1 part by weight per 100 parts by weight oforganopolysiloxane (A), comprising an alkanol having 1 to 4 carbon atomsand, optionally, water, with

(C) 0.05 to 5 parts by weight of the solubilizing agent described aboveper 100 parts by weight of organopolysiloxane (A).

The cloudy mixtures of components (A) and (B) become clear again by thisprocedure.

The C₁ - to C₁₉ -carboxylic acid C₁ - to C₁₂ -alkyl esters and -glycolesters (C1) employed as the solubilizing agent (C) preferably have theformula ##STR2## in which R⁷ is a C₁ - to C₁₈ -alkyl radical,

R⁸ is a hydrogen atom or a C₁ - to C₆ -alkyl radical,

k has the values 1, 2 or 3 and

l has the values 0 or 1 to 20.

R⁷ is preferably straight-chain and has 1 to 19 carbon atoms. R⁸ ispreferably a straight-chain alkyl radical and has 1 to 6 carbon atoms. kpreferably has the value 2. The value of 1 is preferably 0 or 1 to 5.

The C₃ - to C₂₀ -alkanols and C₃ - to C₂₀ -alkanol-C₁ - to C₁₂-alkoxylates (C2) preferably have the formula

    R.sup.7 --CH.sub.2 CH.sub.2 --[O(CH.sub.2).sub.k ].sub.u OH (IX)

u has the values 0 or 1 to 20 and

k and R⁷ have the above meanings.

R⁷ preferably has 4 to 14 carbon atoms.

The organosilicon compounds (C3) containing glycoside radicals arepreferably built up from units of the formula ##STR3## in which v hasthe values 0, 1, 2 or 3,

o has the values 0, 1, 2 or 3 and

R⁹ is a radical of the formula

    Z--[(CH.sub.2).sub.k O].sub.u --R.sup.2 --                 (XI)

wherein

Z is a glycoside radical which is built up from 1 to 10, preferably 1 to4, in particular 1 or 2, monosaccharide units and

R¹, R², k and u have the above meanings, with the proviso that the sumof v and o is less than or equal to 3, and the organosilicon compound ofunits of formula (X) contains at least one radical R⁹ per molecule.

Examples of monosaccharides from which the glycoside radicals Z can bebuilt up are hexoses and pentoses, such as glucose, fructose, galactose,mannose, talose, allose, altrose, idose, arabinose, xylose, lyxose andribose, glucose being more preferred.

Examples of alkylene radicals are methylene, ethylene, propylene,butylene, pentylene, hexylene, heptylene, octylene, nonylene, decyleneand octadecylene radicals.

The radical R² is preferably linear alkylene radicals having 2 to 20carbon atoms, more preferably linear alkylene radicals having 2 to 8carbon atoms, in particular the n-propylene radical.

Examples of radicals R⁹ are G--CH₂ CH₂ CH₂ --, G--(CH₂ CH₂ O)--CH₂ CH₂CH₂ --, G--(CH₂ CH₂ O)₂ --CH₂ CH₂ CH₂ --, ##STR4## in which G is aglucoside radical (C₆ H₁₁ O₆ --), ##STR5## in which G₂ is a glycosideradical built up from two glucose units.

The radical R⁹ is preferably G--CH₂ CH₂ CH₂ --,

G--(CH₂ CH₂ O)--CH₂ CH₂ CH₂ --,

G₂ --CH₂ CH₂ --CH₂ --,

and

G₂ --(CH₂ CH₂ O)--CH₂ CH₂ CH₂ --,

where

G--(CH₂ CH₂ O)--CH₂ CH₂ CH₂ --,

and

G₂ --(CH₂ CH₂ O)--CH₂ CH₂ CH₂ --, are more preferred and G is aglucoside radical (C₅ H₁₁ O₆ --), and G₂ is a glucoside radical built upfrom two glucose units.

The organosilicon compounds containing glycoside radicals are preferablythose of the formula

    R.sup.9.sub.q R.sup.1.sub.3-p SiO--[(SiR.sup.1 R.sup.9 O).sub.r --(SiR.sup.1.sub.2 O).sub.s ].sub.t --SiR.sup.1.sub.3-q R.sup.9.sub.x (XII)

in which

R¹ and R⁹ have the above mentioned meaning,

q is 0 or 1,

r is 0 or a number from 1 to 200, preferably 0 or a number from 1 to100, more preferably 0 or a number from 1 to 50,

s is 0 or a number from 1 to 1000, preferably 0 or a number from 1 to500, more preferably 0 or a number from 1 to 100 and

t is 0 or a number from 1 to 1200, preferably 0 or a number from 1 to600, more preferably 0 or a number from 1 to 100,

with the proviso that the compound of formula (XII) contains at leastone radical R⁹.

If r in the organosilicon compounds containing glycoside radicals, offormula (XII), is on average other than 0, q is preferably 0.

If x in the organosilicon compounds containing glycoside radicals, offormula (XII), is on average other than 0, r is preferably 0.

Although not shown by formula (XII), up to 10 mole % of thediorganosiloxane units can be replaced by other siloxane units, such asR¹ SiO_(3/2), R⁶ SiO_(3/2) and/or SiO_(4/2) units, in which R¹ and R⁶have the above meaning.

The optically clear compositions can also comprise basic catalysts andacidic catalysts which promote the condensation and the equilibrationreaction. Examples of basic and acidic catalysts are alkali metalhydroxides, in particular potassium hydroxide and cesium hydroxide,alkali metal alcoholates, quaternary ammonium hydroxides, such astetramethylammonium hydroxide, benzyltrimethylammonium hydroxide andbenzyltriethylammonium hydroxide, benzyltrimethylammonium butylate,β-hydroxyethyltrimethylammonium 2-ethylhexoate, quaternary phosphoniumhydroxides, such as tetra-n-butylphosphonium hydroxide andtri-n-butyl-3-[tris-(trimethylsiloxy) silyl]-n-propylphosphoniumhydroxide, alkali metal siloxanolates and ammonium organosiloxanolates,such as benzyltrimethylammonium methylsiloxanolate, hydrofluoric acid,boron fluoride and ammonium fluorides such as cetylamine hydrofluoride.

The basic catalysts and acidic catalysts which promote the condensationand the equilibration reaction can already be mixed with the compounds(E) and (F) during preparation of the optically clear compositions.Preferably, not more than 5, in particular not more than 2, parts byweight of basic or acidic catalysts are present per 100 parts by weightof organopolysiloxane (A) or compounds (E) and (F).

The optically clear compositions can comprise additives for particularpurposes, for example for use as textile treatment compositions, inaddition to the above constituents. Suitable additives are biocides,such as fungicides, bactericides, algicides and microbicides,thickeners, antifreezes, antistatics, dyestuffs, flameproofing agentsand organic plasticizers.

In the following examples, unless stated otherwise in each case,

a) all the amounts data are based on the weight;

b) all the pressures are 0.10 MPa (absolute);

c) all the temperatures are 20° C.

EXAMPLE 1

In each case 98 parts by weight of a polydimethylsiloxane oil withterminal hydroxyl groups and having a viscosity of 70 mPa. s at 25° C.were mixed with 2 parts by weight of a silane of the formula

    CH.sub.3 (CH.sub.3 O).sub.2 SiY                            (XlII)

and the mixture was stored at 20° C. After the time stated below,clouding occurred.

Silane 1:Y=--(CH₂)₃ --NH(CH₂)₃ CH₃ ; clouding after 17 days.

Silane 2:Y---(CH₂)₃ --NHCH₃ ; clouding after 10 days.

Silane 3:Y=--(CH₂)₃ --NH--(CH₂)₃ --OCH₃ ; clouding after 24 days.

Silane 4:Y=--(CH₂)₃ --NH--(CH₂)₂ --N(CH₃)₂ ; clouding after 20 days.

Silane 5:Y=--(CH₂)₃ --NH(cyclohexyl); clouding after 20 days.

Silane 6:Y=--(CH₂)₃ --NH--(CH₂)₂ --NH₂ ; clouding after 21 days.

Two days after clouding had occurred, the mixtures were mixed with 1part by weight of iso-tridecyl-diethylene glycol ether. The mixturesbecame optically clear after a few minutes.

EXAMPLE 2

The mixtures prepared in Example 1 were mixed with 10 parts by weight ofiso-tridecanol 2 days after clouding had occurred. The mixtures becameoptically clear after a few minutes.

EXAMPLE 3

The mixtures prepared in Example 1 were mixed with 10 parts by weight ofiso-propyl palmitate 2 days after clouding had occurred. The mixturesbecame optically clear after a few minutes.

EXAMPLE 4

The mixtures prepared in Example 1 were mixed with 10 parts by weight ofethylglycol acetate 2 days after clouding had occurred. The mixturesbecame optically clear after a few minutes.

EXAMPLE 5

In each case 98 parts by weight of a polydimethylsiloxane oil withterminal hydroxyl groups and having a viscosity of 70 mPa.s at 25° C.were mixed with 2 parts by weight of the silane 6 described in Example 1and with the solubilizing agents stated in Examples 1 to 4 above, in theamounts stated, and the mixture was stored at 20° C. for 40 days. Themixtures remained optically clear.

What is claimed is:
 1. An optically clear composition comprising(A) anorganopolysiloxane which contains at least one monovalent SiC-bondedradical with primary, secondary and/or tertiary amino groups, (B) 0.01to 1 part by weight per 100 parts by weight of organopolysiloxane (A) ofcompounds from a group consisting of water, methanol and ethanol and (C)0.05 to 20 parts by weight of a solubilizing agent per 100 parts byweight of organopolysiloxane (A), chosen from a group consisting of(C1)C₁ - to C₁₉ -carboxylic acid C₁ - to C₁₂ -alkyl esters and -glycolesters, (C2) C₃ - to C₂₀ -alkanols and C₃ - to C₂₀ -alkanol-C₁ - to C₁₂-alkoxylates and (C3) organosilicon compounds containing glycosideradicals.
 2. An optically clear composition as claimed in claim 1, inwhich the organopolysiloxane (A) contains at least one siloxane unit ofthe formula

    R.sup.1.sub.a Q.sub.b SiO.sub.(4-a-b)/2                    (I)

and all other siloxane units have the formula

    R.sup.1.sub.c SiO.sub.(4-c)/2                              (II)

in which R¹ is identical or different monovalent optionally fluorine-,chlorine- or bromine-substituted C₁ - to C₁₈ -hydrocarbon radicals,hydrogen atoms, C₁ - to C₁₂ - alkoxy or hydroxyl radicals or alkylglycolradicals, Q is a group of the formula

    --R.sup.2 --[NR.sup.3 (CH.sub.2).sub.m ].sub.d N(R.sup.3).sub.2 (III)

in which R² is a divalent C₁ - to C₁₈ -hydrocarbon radical, R³ is ahydrogen atom or an optionally fluorine-, chlorine- or bromine- or C₁ -to C₅ -alkoxy-substituted C₁ - to C₁₈ -hydrocarbon radical, a has thevalues 0, 1, or 2, b has the values 1, 2 or 3, c has the values 0, 1, 2or 3, d has the values 0, 1, 2, 3 or 4 and m has the values 2, 3, 4, 5or 6 and the sum of a+b is not more than
 4. 3. An optically clearcomposition as claimed in claim 1, wherein the amine content oforganopolysiloxane (A) is from 0.01 to 2 meq/g, measured as theconsumption of 1N hydrochloric acid in ml/g during titration to theneutral point.
 4. A process for the preparation of an optically clearcomposition as claimed in claim 1, in which(E) compounds which arechosen from(E1) organosilanes which contain at least one monovalentSiC-bonded radical with primary, secondary and/or tertiary amino groupsand at least one C₁ - to C₄ -alkoxy group and (E2) organopolysiloxaneswhich contain at least one monovalent SiC-bonded radical with primary,secondary and/or tertiary amino groups and at least one C₁ - to C₄-alkoxy and/or silanol group and (F) compounds which are chosen from(F1)organosilanes which contain at least one C₁ - to C₄ -alkoxy group and(F2) organopolysiloxanes which contain at least one C₁ - to C₄ -alkoxygroup and/or silanol groupare reacted as starting compounds in thepresence of (C) 0.01 to 20 parts by weight of the solubilizing agent per100 parts by weight of the starting compounds (E) and (F).
 5. A processfor the preparation of an optically clear composition as claimed inclaim 1, in which(A) an organopolysiloxane which contains at least onemonovalent SiC-bonded radical with primary, secondary and/or tertiaryamino groups and (B) 0.01 to 1 part by weight per 100 parts by weight oforganopolysiloxane (A) consisting essentially of an alkanol having 1 to4 carbon atoms and, optionally, water are mixed with (C) 0.05 to 5 partsby weight of the solubilizing agent per 100 parts by weight oforganopolysiloxane (A).
 6. An optically clear composition as claimed inclaim 1, wherein the C₁ - to C₁₉ -carboxylic acid C₁ - to C₁₂ -alkylester or -glycol ester (C1) having the formula ##STR6## in which R⁷ is aC₁ - to C₁₈ -alkyl radical,R⁸ is a hydrogen atom or a C₁ - to C₆ -alkylradical, k has the values 1, 2 or 3 and l has the values 0 or 1 to 20.7. An optically clear composition as claimed in claim 1, wherein theC₃ - to C₂₀ -alkanol or C₃ - to C₂₀ -alkanol-C₁ - to C₂ -alkoxylate (C2)having the formula

    R.sup.7 --CH.sub.2 CH.sub.2 --[O(CH.sub.2).sub.k ].sub.u OH (IX)

u has the values 0 or 1 to 20 and k has the values 1, 2 or 3, and R⁷ isa C₁ - to C₁₈ -alkyl radical.
 8. An optically dear composition asclaimed in claim 1, wherein the organosilicon compound (C3) containingglycoside radicals is built up from units of the formula ##STR7## inwhich v has the values 0, 1, 2 or 3,o has the values 0, 1, 2 or 3 and R⁹is a radical of the formula

    Z--[(CH.sub.2).sub.k O].sub.u --R.sup.2 --                 (XI)

wherein Z is a glycoside radical which is built up from 1 to 10,monosaccharide units and R¹ is identical or different monovalentoptionally fluorine-, chlorine- or bromine-substituted C₁ - to C₁₈-hydrocarbon radicals, hydrogen atoms, C₁ - to C₁₂ - alkoxy or hydroxylradicals or alkylglycol radicals, R² is a divalent C₁ - to C₁₈-hydrocarbon radical, is a hydrogen atom k has the values 1, 2 or 3, andu has the values 0 or 1 to 20 and with the proviso that the sum of v ando is less than or equal to 3, and the organosilicon compound of units offormula (X) contains at least one radical R⁹ per molecule.